It’s funny when middle-class white people try to rap. It’s funny when they listen to rap (see: the gridlock scene in Office Space) and it’s funny when they turn hardcore rap songs into piano ballads (such as Ben Folds’ 2005 cover of Dr. Dre’s “Bitches Ain’t Sh—t”). Andy Samberg’s comedy team The Lonely Island is particularly skilled at exploring the dichotomy between the middle-class American lifestyle and the kind of thuggish, grandstanding music that originated in the streets. Or at least that’s what I read somewhere. I just think it’s funny when Natalie Portman smashes things.

The Lonely Island’s new album Turtleneck & Chain comes out May 10. On it, Samberg’s crew has expanded its gangsta prep repertoire to include glitzy sleazebag dance anthems. They debuted the hilariously lame single “Jack Sparrow” on last weekend’s Tina Fey-hosted episode of Saturday Night Live. The song features an amazing cameo by Michael Bolton. No, I’m serious. Michael Bolton is great. He’s even wearing khakis.

Sometimes it’s difficult to categorize The Lonely Island’s work—their 2009 hit “I’m on a Boat” was nominated for a rap Grammy, but lost out to the actual hip-hop song, “Run This Town,” by Jay-Z, Rihanna and Kanye West. The group’s musical creations are more than just novelty songs but somehow less than what anyone would consider actual music. They’re sort of the Pottery Barn version of Spinal Tap.